


no rest for the wicked

by wiltedfeathers



Category: Supernatural
Genre: Character Death, Depression, F/M, I'm sorry for what you're about to read, Major Character Undeath, Miscarriage, Mutual Pining, Porn With Plot, References to Depression, Repressed Emotions, Unplanned Pregnancy, absolutely no happy endings here, bobby singer is truly the only rational character on this show, by now we all know dean went to hell and came back, dean 'I'm irrational and impulsive' winchester, just OPEN UP or buy a JOURNAL god, let me take you down another hole of angst, lots of trips to the hospital, reader's not grieving well
Language: English
Status: Completed
Published: 2020-10-26
Updated: 2020-11-09
Packaged: 2021-03-09 01:07:39
Rating: Mature
Warnings: Major Character Death, No Archive Warnings Apply
Chapters: 3
Words: 5,246
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27205652
Author URL: https://archiveofourown.org/users/wiltedfeathers/pseuds/wiltedfeathers
Summary: “It was... It’s...” Dean sucked in a breath. “It’s complicated. You wouldn’t understand.”You scoffed, causing Dean to look at you for the first time all night.“You think I don’t know complicated when it comes to you? I’ve been tagging along with you and Sam for god knows how long.”
Relationships: Dean Winchester/You
Kudos: 23





	1. Chapter 1

**Author's Note:**

> not too long ago I was off the benadryl and brainstormed a mini fic based around dean going to hell and thought about it for 3 days straight
> 
> timeline wise it's end of s3/start of s4

It was late. It was also really hard to get a good night’s sleep in a house full of hunters. 

You threw yourself out of bed with a frustrated groan and a yawn as you pulled on a hoodie, feet finding a pair of shoes as you headed down to the kitchen for a glass of water. Bobby’s house being a mess was a given considering his profession but it seemed more of a hazard, a spooky one at that, in the middle of the night with the lone light source coming from a room down the hall. You assumed the boys were going over their plans for the next hunt so you didn’t want to disturb them or be too loud, opting to take the water to-go back to the room you were staying in.

It was Sam’s voice that caught you off guard and froze you in your tracks.

“Dean, you’ve known about this deal for a year and you haven’t told her?” His voice was loud enough to make you jump. “You’ve got less than twenty-four hours to live!”

Your heart stopped and your hands began to tremble, causing you to drop the glass that was in your hands. You’ve known Dean long enough that you were used to his usual reckless decisions but he couldn’t be _that_ fucking stupid, right?

You barely noticed the broken glass at your feet, nor did you notice the three men staring at you. Silence blanketed the room but it spoke volumes, and the fact that Dean couldn’t look you in the face was confirmation enough. Anxiety ran through your veins as your brain pieced together the context clues to come to a conclusion you hoped was a lie.

“Tell me you didn’t make a deal.” Your tone was soft yet loud enough for the men to hear. 

The room was tense and Dean still couldn’t look at you. In his words, or lack thereof, was a confirmation.

“You’ve gotta be kidding me Dean!” Your voice was raised, loudest any of the men had heard before. The anxiety of it all had faded into adrenaline and rage, the eldest Winchester not even flinching at your tone. Your eyes brimmed with tears and before anyone could interject you had stormed off back to your room, swiftly locking the door behind you and sliding down to the floor in tears. 

Dean was the love of your life and he didn’t even know it and in less than a day you were gonna lose him.

A soft knock on the door had snapped you back to reality. You lost track of how much time had passed even though at most an hour had gone by, and you were half hoping that it was Sam or Bobby on the other side.

“Who is it?” Your voice was hoarse from crying for so long that it was almost too painful to talk.

“It’s Dean.”

You didn’t know if you wanted to comfort him or kill him, but it took everything in you to not choose the latter.

“Go away.” You responded.

“Please just let me explain.”

Your soft spot for him always managed to take over at the worst times. You unlocked the door with a sigh, eyes still blurry with tears as you looked at the hunter. He had a look on his face that was a mix of somber guilt, avoiding any kind of eye contact with you as he stepped past you. 

“I don’t know where to begin.” He broke the awkward silence, keeping his gaze laser focused out the window.

“You can start by explaining why you lied to me.” You wiped your eyes before leaning against the door with your arms crossed, staring at the designs in the carpet.

A pause.

“It was... It’s...” Dean sucked in a breath. “It’s complicated. You wouldn’t understand.”

You scoffed, causing Dean to look at you for the first time all night.

“You think I don’t know complicated when it comes to you? I’ve been tagging along with you and Sam for god knows how long.” There was a hurt tone to your voice and your eyes started to sting with tears again. “I just don’t understand how you could lie to me about making a deal with a demon, of all the fucking things in the world.”

“I didn’t ask you to!” Dean’s raised voice had caught you off guard. “Sam and I didn’t want this for you. You could’ve had a normal life like everyone else but-“

“But what Dean?” You interrupted, not bothering to hold back your tears. “I’ve never been a problem before but now you’re blaming me because _you_ chose to hide this. _You_ kept your demon deal a secret and I’m finding out the day before you meet the man downstairs?”

“I kept it a secret because I’m in love with you, okay? You happy?”

Silence.

The two of you just stared at each other.

“Fuck, I mean, you saw how fucked up I was after I thought I lost Sammy for good; you were there!” Dean ran a hand over his face before sitting on the bed. “I did what I had to do to bring him back. It’s my job to protect him and I just let him die.”

“What does that have to do with you being in love with me?” You were full on crying at this point and you didn’t care. “You don’t lie to people you claim to love.”

“Because it wasn’t fair to you.” His tone was quieter as he looked at you, guilt hitting him straight in the chest at the sight of your teary face. “It wasn’t fair to bring it up knowing I had a year left and by the time I realized how I felt about you I knew there wouldn’t be enough time for us to even try. I didn’t want to take things, especially you, for granted.”

Your entire perspective shifted. Anger melted into remorse as you processed his words, yet again wiping your arms and sniffing.

Silence.

Dean held his head in his hands and you could see him tremble. He was rarely this vulnerable with you without alcohol, so you knew this was eating him up inside. He was scared and it showed.

“I thought I was protecting you by not saying anything. I’m sorry. I know it’s not gonna fix things, but I’m sorry.”

You walked over to the bed and stood in front of him and he didn’t hesitate to wrap his arms around you, hiding his face in your shirt. 

“Since we’re being honest now I love you too Dean. Always have.” You broke the silence. “It’s why I was so caught off guard about you lying to me but I understand why you did it and you’re right, nothing about this is fair. We deserve better.”

“Yeah we do.” Dean looked up at you and you both just stared at each other. You thumbed his tears away as you took in his features for the last time, him leaning into your hand as you cupped his face. He looked up at you in awe, not letting himself ruin the moment by dwelling on the “what ifs”; instead he stood to capture your lips with his own, cupping your face with such care and gentleness that he was scared one wrong move would shatter you into pieces.

It didn’t take long for instinct to take over.

Dean’s hands moved to your hips and pulled you flush against him, fingers tightening their grip as if to keep you in place. Your hands snaked up his shirt and you raked your nails down his front, earning a hiss from the hunter. Dean broke the kiss to peel off your shirt, pulling you on top of him as the two of you fell on the bed. He kissed down your jaw and your neck as your worked to undo his pants, raising your hips as he shimmied off his jeans and boxers.

A hand slipped between your thighs as you pushed your own shorts down, Dean capturing your gasp in a kiss. You moaned against his lips as he slid a finger into your core, then a second, and you were falling apart on top of him. He kissed your temple as he found your sweet spot, thumb circling your sensitive nub as you whimpered against the skin of his neck.

The loss of his fingers caught you off guard and the both of you made eye contact, Dean looking you in the eyes as a final consent and you responded with a nod, both of you letting out a simultaneous sigh of relief and satisfaction. You kissed each other messily as Dean began to rock his hips up into you, his arms wrapped around you tight. His groans filled your ears as your hips rocked down against him.

It wasn’t long after that you both came up and down from your highs, curled into each others. You both were so lost in each other that you ended up losing track of time, the faint soft light of the sun starting to peer in through the windows.

It was somber as the realization of what today meant dawned on the two of you, trying to make the most of your moments in bed together.

Silence.

“I’m not ready to go.” Dean mumbled into your hair. 


	2. Chapter 2

You and Dean had barely exchanged more than a sentence after last night. He wasn’t in your room the following morning and you weren’t even sure if he was still in the house. It’s not like you were the least bit surprised by his actions; if you had less than fifteen hours to live, you wouldn’t want to speak to anyone either. You brushed it off as you dragged yourself to the bathroom to freshen up, then downstairs to scavenge for food and get debriefed by Bobby on the plan for later.

There was a last-ditch effort to go after Lilith and try and free Dean from his deal but much like previous hunts with the Winchesters, it was a job based on sheer hope and fear alone. 

You weren’t counting on being face to face with Dean in the kitchen, freezing as the two of you made eye contact. He cleared his throat before looking down at his hands, holding out a mug to you.

“I assume you came down for coffee.” He said. You nodded and took the cup from him, frowning as you looked into the cup. He had made it just the way you wanted and even though you tried - and failed - to not think about how much you’d miss him, this was just another thing on the list. 

You were barely paying attention during Bobby’s debrief but you had gotten the gist of things; kill Lilith and try not to get yourself or worse, Dean, killed. There were reasons that you barely went on hunts and your worry for both Winchesters was the main one. You knew your way around a gun and a knife and you had killed your fair share of demons and as overwhelming as things were, if the boys needed an extra set of hands you were there.

Much like everyone else you put your fears and worries on the backburner in order to get the job done, however the uneasiness was prominent in the pit of your stomach and Ruby’s presence didn’t make you feel any better. There was something about her that was off and you’d picked up on it from day one. You and Dean could yell at Sam until you both were blue in the face but the younger of the two refused to listen, and unlike Dean, you refused to press him further.

It felt as if you were on autopilot as the group of you walked in, not even noticing Bobby trying to get your attention.

“You good?” He asked, nudging you. “You can sit in the car if you want.”

“Out there? With the demon bitch army?” You gestured, earning a nod from the older man.

“Good point.” Bobby said. “Help me salt these windows.”

Sam, Dean, and Ruby had scanned the house for any sight of Lilith while you and Bobby had kept watch. There was no way that the demon army would bypass sprinklers spraying holy water, but with Lilith there was no taking chances.

The group of you, minus Bobby who stayed back to keep watch, convened in the living room. 

“I’ll do it.” Sam piped up. Both you and Dean looked at him in confusion, and the younger Winchester was laser focused on Ruby.

“What do you mean?” The demon asked.

“To save Dean.” Sam responded. “What do you need me to do?”

“Absolutely fucking not.” You and Dean both said in unison, pausing to look at each other before you averted your gaze to the floor.

“There’s no more time Sam.” Ruby spoke and you stared her down hard. Something wasn’t right about this. “You can’t just flip a switch. We needed time.”

“Sam-” Dean stepped forward.

“No Dean! I’m not letting you go to hell.” 

“Yes, you are!” Dean yelled, causing the room to go silent. “Yes, you are. I mean, this is all my fault. I know that. I fucked up.”

The brothers looked at each other with teary eyes and you swallowed back tears of your own as they continued.

“What you’re doing Sam, it’s not gonna save me. It’s only gonna kill you.”

“Then what am I supposed to do?” Sam asked, gesturing between himself and you. “What are _we_ supposed to without you, Dean?”

The older brother sighed as he looked between Sam and you, running a hand over his face like he always does when he’s indecisive. You couldn’t break your gaze with the floor because you knew if you did you’d burst into tears. There was a time and place for tears which is something you learned quick from hanging around the boys for as long as you have. Dean’s shoes soon came into view and you felt his hand cup your cheek. Your vision was suddenly blurry and as soon as he rested his forehead against yours, the tears finally fell.

“I’m sorry.” He said quietly. 

“Dean… don’t....” You sniffed. He pressed a kiss to the top of your head as the clock chimed, feeling his tears hit the top of your head. You let out a breath as you finally looked at each other for the last time, and he looked back at Sam who was full on crying at this point. 

“I’m sorry Dean.” Ruby spoke. “I wouldn’t wish this upon my worst enemy.’

Panic started to rise at the distant sound of growling and snarling. You and Sam looked at each other in confusion before looking at Ruby, then Dean.

“Hellhound.” Dean said quietly.

“Where?” Sam asked. Dean was looking towards the dining room where the hellhound was, with him and Ruby being the only ones who could see it. He stepped in front of you protectively before it started barking and charging at all of you. As if on cue you all ran to the nearest room, Sam and Ruby scrambling to hold the door as Dean spilled the contents of the hex bag in front of the door. You, on the other hand, were practically hyperventilating. Dean rushed over to hold you and calm you down as best he could, with what little time he had. 

It wasn’t helping.

You weren’t hyperventilating because of Dean, your gaze laser focused on the demon in front of Sam.

“Sam, that’s not Ruby!” You yelled. As the realization dawned on him he was flung to the wall, Dean flung to the table, and Ruby - now Lilith - had you in a chokehold.

“You let her go you bitch!” Dean yelled. “You already got me. Don’t fucking hurt her.”

“Oh, I wouldn’t _dare_ harm a hair on her pretty little head.” Lilith taunted him with a smile, running a finger along your cheek as you tried to move away from her grasp. “But what fun would that be? You’re already going to hell.”

The sharp pain in your side didn’t register until you saw both Winchester’s faces scrunch up with both anger and fear. You let out a bloodcurdling scream as you realized Lilith had stabbed you with the knife before flinging you against the wall next to Sam. Dean was looking in your direction with tears in your eyes, mouthing an ‘I’m sorry’ as you continued to groan in pain. Your vision was growing blurrier between the tears in your eyes and almost passing out from the pain, and the last thing you remember was calling out for Dean before the hellhound sliced him up and everything went black.

When you woke up again it was bright white. At first you believed it was heaven and that you finally bit the bullet, that is, until you heard Bobby’s voice and your vision started to get clearer.

“Sam, she's waking up.” He said, the two of them scrambling to your bedside. 

You were in the hospital. 

As you moved to sit up you started coughing and Sam rushed to give you a cup of water, which you gladly accepted.

“What the fuck happened?” You asked after taking a sip, resting your head against the pillows. It was quiet as Sam and Bobby hesitated, exchanging looks before looking at you.

“What do you remember?” Bobby asked.

“Not much.” You took another sip of water. “I remember Lilith and being up against the wall, and Dean…

Fuck. 

Dean was in hell. 

“Yeah…” Bobby spoke. Sam was dead silent. “The hellhound got him. According to Sam, Lilith stabbed you with the knife. You should be dead right now.”

You gave Bobby a look. 

“No offense.” He threw his hands up in defense and you took another sip of water. As if on cue, the doctor had walked in. 

“Oh, you’re awake! Good.” The doctor spoke as he looked over his clipboard. “Must have had a hell of a car accident. You were out for weeks.”

“Weeks?” You asked.

“Yeah. Lost a lot of blood too.” He let out a whistle as he gave your chart a once-over. “It’s a miracle you’re still alive and didn’t lose the baby.”

“Baby?” Bobby, Sam, and you spoke in unison. “What baby?”

“Yeah, you’re about a month along. Congratulations!” The doctor nodded at you and Sam before walking off. Bobby looked between the two of you in confusion.

“Is there something you two wanna tell me?” Bobby asked, eyebrow raised in confusion.

“It’s not me, I swear.” Sam held up his arms in defense before crossing them, a somber look crossing both his and Bobby’s faces as they realized.

“It’s Dean’s.” You mumbled. 


	3. Chapter 3

**Notes for the Chapter:**

> you ever just accidentally write a 2k chapter? me too
> 
> thank you for joining me on this impulsive journey of angst i genuinely didn't know how to end it but i didn't wanna drag it out longer than intended i hope you guys enjoy either way!

Adjusting to normal life after losing Dean wasn’t the easiest thing in the world.

Losing the love of your life and learning that you were carrying his child in a span of twenty-four hours only sent you into a downward spiral of grief. After being discharged from the hospital you holed yourself up in one of Bobby’s spare rooms, slowly becoming a shell of your former self. Bobby and Sam did what they could to make sure you were taken care of by leaving food and water outside your door, checking in from time to time as frequently as they could. Sometimes Sam would just sit in the room with you to make sure you weren’t alone, even if there were barely, if at all, any words exchanged. 

You couldn’t bring yourself to be there for Dean’s burial. The guilt of everything had weighed on you to the point where you didn’t even know if you were human anymore. 

Why did you wait so long to express your feelings to him? Why did you tag along on that job if you knew the outcome would change? Why did you let yourself get caught up with the Winchesters in the first place? 

Hell, you even felt guilty knowing you were carrying Dean’s child and he wouldn’t be alive to watch them grow up. 

By the time Bobby and Sam returned they found you passed out on the floor of the room with an empty bottle of tequila next to you and by the time you woke up, you were right back where everything started: the hospital. 

There was a silent understanding but it didn’t shake the disappointment that oozed from the two hunters. 

Somehow you already knew the bad news before the doctor had walked in to deliver it. A somber feeling draped the air once he walked out. The word repeated in your head on a loop; ‘ _ Stillborn _ ’. 

After a week you were discharged and back at Bobby’s. Sam had gone off to god knows where as you and Bobby adjusted to a new reality without the Winchesters. You distracted yourself as much as you could whether it be helping the elder hunter with research or tidying up around the house, even going as far as teaching yourself how to tune up old cars out in the yard just to simply get some fresh air and be out of the house. 

Over time you eased into a period of acceptance. It was quieter without the brothers, almost surreal but for the first time in your life you felt a sense of peace. You realized that Sam leaving was his form of grieving and Dean was simply dealing with the consequences of his deal with a demon. There was nothing that could change the course of events or make the pain any worse than it already was.

At least that’s what you thought.

It was exactly four months to the day of losing Dean and there was something off about the day, and not the usual off feeling that you usually got. The brothers always told you your intuition was a gift.

There were crashes coming from the house so loud that you heard it all the way outside in the shed. You rolled yourself from under the car you were tinkering with, wiping your hands on your shirt before grabbing the closest tool you could for a makeshift weapon. The crashes and yelling got louder as you made your way to the house, wrench in baseball bat position as you sneaked in through the back door. You snuck into the kitchen where Bobby was staring down the man standing in front of him, the older male’s face shifting into an expression of panic once you made eye contact.

The second male turned around to follow Bobby’s gaze and you looked as if you’d seen a ghost.

It was Dean.

You didn’t know if you wanted to fall into his arms and cry or send him back six feet under. 

He walked over to you slowly as you dropped the wrench in your hands, eyes glossing over with tears as you took him in. Four months without him and he was standing right in front of you like he never even died.

Before he could speak your fist had made contact with his jaw and Bobby was rushing over to hold you back.

“It’s him! It’s really him!” Bobby had yelled as you attempted to charge at him. “I triple checked. It’s him. No tricks.”

Confusion, disbelief, and god knows how many other emotions were flowing through you as you stared at Dean. You convinced yourself he was dead, taking Sam and Bobby’s word for it; especially Sam’s, as he had watched his brother die with his own eyes.

Bobby had let you go and stepped out of the way once he sensed you were calm enough, walking over to the fridge to get Dean ice for his face. 

“I’ll leave the two of you two it then.” The older male wiped his hands before walking out of the room. Somehow, that made things more awkward than they were. Silence blanketed the room as you tried to focus your gaze on anything but Dean, but you were in such disbelief that you couldn’t stop staring, nor could you find the right words.

“I know what you’re gonna ask and I don’t know why or how, but I’m here.” He said.

“You think that’s supposed to make me feel better?” There was bitterness in your voice. “You can’t just show up out of the blue like you didn’t just fucking die!”

“If it makes you feel any better I’m not a demon.” He shrugged. You rolled your eyes and stormed off to your room, Dean not even budging to try and stop you or make an effort to explain himself. He heard a distant slam of a door and sighed to himself, brushing the interaction off in favor of finding Bobby.

* * *

Hours had passed and you barely noticed as you’d spent most of that time crying. Months ago you would’ve begged for anything to bring Dean back but seeing him in person only re-opened the wound, leaving you the same emotional wreck you were when you lost him. 

Dean Winchester. Always leaving you in tears regardless if the situation was good or bad, and the bad always managed to outweigh the good.

A gentle knock on the door pulled you out of your thoughts. You built up the strength, emotional and physical, to bring yourself to answer it. Part of you wished you hadn’t, as you were face to face with Dean for the second time that day.

“What do you want?” You asked.

“To talk.” He said. 

“I don’t wanna talk.” You rolled your eyes and attempted to close the door behind you. Dean had stopped it with his foot, stepping in the room before closing and locking it behind him.

“I do.” His tone wasn’t as harsh as it usually was and there was no hint of sarcasm to his voice. It felt as if he was genuinely sincere and that scared you. “Look, I know there’s nothing I can do or say that can undo the last four months or make things better, but I want to try.”

A pause. 

“I don’t know what you want me to say, Dean.” Your gaze had shifted from the floor to the wall as you sat on the wall. “I just spent the last four months grieving over you and all of a sudden you’re back like you never even died.”

“I know.” He sighed, rubbing a hand over his face. “I’m sorry for ever making that damn deal in the first place but I… I just couldn’t let Sammy die. It’s my job to protect him and I… I couldn’t live with myself if…”

“Yeah, I get it.” You said. 

Another pause. A long one.

“Do you remember anything? I mean… from that night...” You finally spoke up.

“Not really, no.” He said, shrugging. “It’s all a blur. Last I remember was Lilith and the next thing I knew I was digging myself out in some random forest in Pontiac. I’m guessing you didn’t go to my funeral.”

“No, I… I don’t remember that day, honestly.” You half-lied. Due to your little… bender, that day was all a blur but as much as you tried to block it out, you couldn’t. “I was in the hospital actually.”

“Hospital?” There was concern in Dean’s voice as he adjusted himself to face you, eyebrows raised in disbelief. “You were in the hospital?”

“Twice.” You glanced at him once you noticed his position changed, feeling more anxious than you did when he walked in. “The night you died Lilith had stabbed me before she sicced her hellhound on you. I lost so much blood I ended up in a coma.”

Dean’s heart stopped at the mention, let alone the thought of you in harm’s way at his watch. Even the mere mention of knowing Lilith had put her hands on you had caused him to instinctively clench his fists, fighting the rage that was suddenly building up inside of him.

“I shouldn’t have gotten you into this shit.” He sighed to himself.

“It’s my fault.” You finally made eye contact with him, shrugging in response. “I thought I could kill her myself and I paid the price for it.”

Dean took your hands in his own and raised them to his lips, pressing a gentle kiss to the skin. Guilt began to wash over him and he was mentally beating himself up for not being there to protect you.

“Don’t say that.” He spoke, still not letting go of your hands. “I was the one who made that deal and got everyone into this mess.”

He rested his forehead against yours and took a deep breath as he kept his tears at bay. He’d spent all day trying not to break down and he wasn’t planning on stopping now. The two of you sat there to take in the moment, to take in each other’s presence.

However besides the mystery surrounding Dean’s return from hell, there was another elephant in the room that needed addressing.

“I, uh… There’s…” You started, taking a pause to calm yourself down as you moved away from Dean. “There’s something I have to tell you.”

“Sure, yeah.” He sat up and looked at you, hands still holding yours reassuringly. “You can tell me anything.”

You took a deep breath before speaking again, nerves and anxiety getting the best of you. Dean could tell you were shaking and he circled his thumb along the back of your hand, trying his best to calm you down.

“I was pregnant.” You spoke up after a brief pause, noticing Dean tense up at the confession. “The doctor told me once I came out of the coma.”

“...Pregnant?” Dean asked. You nodded.

“Yeah.” With your free hand you wiped your eyes as you began to bounce your leg, anything that could distract you from the memory. “I, uh… I didn’t…”

Dean could barely wrap his head around the idea that you were pregnant, that the two of you would have been parents. He couldn’t wrap his head around the idea that you raised a child without him, that he missed god knows how many milestones. There was something about your mannerisms that tipped him off, something deep in his gut that caused his eyes to tear up.

“You said you were in the hospital twice?” His voice started breaking at the question, clearing his throat. You nodded, expression stoic as the tears rolled down your cheeks.

“I almost drank myself to death the night Sam and Bobby buried you. I woke up in the hospital the next morning and…” You started.

“And?”

You looked at Dean with teary eyes and his jaw clenched, blinking at you a few times before swallowing back his own tears.

“Stillborn.” You said. “I had lost the baby weeks before.

You half-expected Dean to up and walk out of the room in that moment, but what you didn’t expect was him to pull you into his arms. The two of you held each other as you both broke down, releasing every single repressed emotion from the past four months. Hours had passed and the two of you were still tangled up in each other, both sleepy from the amount of tears shed.

“Where do we even go from here?” You asked, breaking the silence.

“I have no fucking idea.” 


End file.
